Taxation of Employee Donated Sick Leave

Even simple acts of kindness, such as donating paid sick leave to co-workers in need, can trigger complex tax requirements. The IRS recently released Private Letter Ruling 200720017 that sheds light on the federal tax consequences of such donations, highlighting the importance of following specific requirements such as employer-sponsored medical leave-sharing arrangements or qualified employer-sponsored…

Can Court Force Taxpayers to Hire Tax Attorney?

Have you ever tried to represent yourself in a legal matter? It’s not easy, and the court usually advises against it. But what happens when a taxpayer repeatedly refuses to hire an attorney and insists on representing themselves in a criminal tax matter? This was the issue at hand in the United States v. Baucom,…

IRS Tax Attorneys Realign Organization Structure

The IRS Office of Chief Counsel employs the IRS’s own tax attorneys.  These attorneys handle most of the civil tax court matters for the IRS.  Whenever the IRS implements changes to its organizational structure or management team for this function, it warrants close attention and analysis from taxpayers, tax professionals, and other stakeholders. Such changes have…

Aggressive State Tax Collections

If you owe back taxes, the general rule is that you pay the state and then negotiate with the IRS. The reason for this is that the states are particularly aggressive when it comes to collecting back taxes. Some states are more aggressive than others. And their practices vary over time. In the event of…

Offer in Compromise Deemed Accepted by the IRS

The IRS consumes volumes of information. It processes this information largely by processing paper forms. This includes paper forms submitted by you, the taxpayer and your tax attorneys, and by internal forms created by IRS employees. This inefficient paper form submission and processing is complemented by an insistence on sending taxpayer notices by mail. The…

Can Taxpayers Withhold Payment Pending Government Response?

As citizens, we sometimes seek answers from the government, be it information about UFOs or more practical questions such as what provision grants the IRS the right to collect taxes. For years, tax protesters have been asking the latter, only to be met with evasive responses from the IRS. The case of We the People…

Prepaying Taxes Before Bankruptcy Filing

Unlike tax laws that establish a specific amount due, bankruptcy laws define what is not due. These conflicting policy objectives can lead to unique outcomes in cases of unpaid taxes. For instance, what happens to taxes held by the IRS but not yet applied to a future tax liability when a taxpayer overpays their taxes…